HCID 89443673, compound → 4-Fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,5-dimethyl-phenol

HRID 1771744Notes

Reaction equation

HRID 1771744 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[C:12]([CH3:13])=[C:11]([OH:14])[CH:10]=[C:9]([CH3:15])[C:8]=1[F:16])=O>C1COCC1>[F:16][C:8]1[C:9]([CH3:15])=[CH:10][C:11]([OH:14])=[C:12]([CH3:13])[C:7]=1[NH:6][CH2:4][C:3]1[CH:17]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:19]=[CH:20][C:2]=1[F:1]

Participants

3

Reactant 1

HCID 89443673HCID 89443673, compound

Product 1

HCID 894451294-Fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,5-dimethyl-phenolYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2-fluoro-N-(2-fluoro-5-hydroxy-3,6-dimethyl-phenyl)-5-(3-fluorophenyl)benzamide (230 mg, 0.62 mmol, 1.0 eq) in THF (3 mL) at 0° C. under N2 was added a solution of BH3 (1M in THF, 3.7 mL, 3.7 mmol, 6.0 eq) dropwise. The reaction mixture was heated at 60° C. overnight. After cooling, the reaction was quenched by addition of water and extracted with EtOAc. The organic extract was washed with aqueous NaHCO3, water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white solid (220 mg, 99%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction was quenched by addition of water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with aqueous NaHCO3, water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-07bdea50ad0942b9859e332ab90b14b2
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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